Okkervil River (solo) and Damien Jurado played City Winery – 10/5

Prolific Pacific Northwest singer-songwriter Damien Jurado and Okkervil River’s Will Sheff brought their co-headlining tour to Boston’s City Winery last week.

In contrast to another recent night out, the showgoing energy in Boston on Tuesday evening felt like something close to normal. Maybe it was the buzz of the Sox/Yankees wildcard game across town, or just the less psychologically-loaded nature of the relatively shiny-and-new City Winery, but the mood was right.

The venue – which offers table service for both its wine list and a full-on food menu, in an experience that essentially boiled down to indie-folk dinner theater on this particular night – is an objectively weird place to see live music. Some ill-timed dropped glasses and scraped chairs aside though, the format worked pretty well for the duo of Jurado and Sheff – two artists I am not averse to drinking a Cabernet with.

On first, seated and joined by a second guitarist/occasional bassist, Jurado delivered a hushed set of heartbreakers to a reverent crowd. Jurado’s imposing back catalog is not one I’ve spent a ton of time with, but it’s certainly one I’m bookmarking for further investigation on the strength of this sampling. The songs are largely not happy ones, which he’d be the first to tell you, but he offset the emotional heavy lifting with humorous anecdotes on offending arboretum patrons with his affection for fake plants and watching fights break out between Sheff’s fans and his own at another bill they’d once shared at the Middle East Downstairs. The Jurado fans and Okkervil heads in the house were less pugnacious this time around, calmed by the years perhaps, and a few shouted song requests were the rowdiest things would get.

I’ve been going to Okkervil River shows for about as long as I’ve been seriously into music, but I’d never managed to see frontman Sheff do the solo acoustic thing at full set length. Powering through some self-professed tour fatigue, he brought both the teeth-gnashing catharsis and softly-strummed melancholy that are key to that catalog to the stage. His songs, now spanning two-plus decades under the Okkervil banner, are not any happier than Jurado’s, but his stage presence was a more spirited one even sans-band.

The setlist pulled primarily from what have emerged as Okkervil’s signature pair of records, 2005’s Black Sheep Boy and its 2007 followup The Stage Names. The former’s “A Stone” is undoubtedly among Sheff’s finest moments as a songwriter, and remains the emotional centerpiece of whatever set it appears in. The latter’s not-oft performed “Savannah Smiles” was a treat batting leadoff in the setlist, as was a rendition of “Famous Tracheotomies” that segued its Ray Davies verse into a full-on “Waterloo Sunset” cover only teased at on the Rainbow Rain recorded version. Another cover – a delightful back-and-forth on “Wichita Lineman” – brought Jurado back to the stage to close out the night (and perhaps unite these two once-warring fanbases for good).

Scroll below for a gallery of both sets.